4-Methylmorpholine → HCID 59822336, compound

HRID 1678525Notes

Reaction equation

HRID 1678525 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([OH:7])=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:21][CH:22]=1)=[O:7]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 757711-HydroxybenzotriazoleHCID 202740913-Bromo-4-(trifluoromethoxy)benzoic acid

Product 1

HCID 59822336HCID 59822336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-4-trifluoromethoxybenzoic acid (515 mg), N-(4-aminophenyl)morpholine (323 mg), EDAC (763 mg), HOBT (538 mg) and N-methylmorpholine (597 μl) in DMF (5 ml) was stirred at room temperature. After 1 h, water (10 ml) was added and the resulting suspension filtered. The residue was dried in vacuo and then purified by flash column chromatography, eluting with 2:1 petroleum ether: ethyl acetate. The title compound was isolated as an off-white solid (532 mg).

Workup

  1. filtrationthe resulting suspension filtered
  2. customThe residue was dried in vacuo
  3. custompurified by flash column chromatography
  4. washeluting with 2:1 petroleum ether

Sources & evidence

ORD record
ord-ed1a0c547057413299392052230f717d
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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